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Ray Leonard retired and came back four times during his career. He originally retired at the very top of his game in 1982, still four years short of 30, citing a damaged retina.
Leonard came back for the first time in 1984, recording a Round 9 TKO of Kevin Howard. Leonard looked far less than spectacular and quickly retired once more.
Then in 1987, Leonard made one of the greatest comebacks in boxing history. After five years almost completely inactive, Leonard came back to face fellow superstar Marvin Hagler for the undisputed middleweight crown. In a close and still-debated fight, Leonard walked away with a split-decision victory.
Leonard followed that by stopping Donny Lalonde to capture the WBC super middleweight and light heavyweight titles, making him a nominal five-division champion. He fought a third fight with Roberto Duran, earning a unanimous decision, and a long-awaited rematch with Tommy Hearns, that went down as a controversial draw which a majority of fans thought Hearns should have won.
Leonard retired for a third time in 1989, only to return in 1991 to face tough young champion Terry Norris. Leonard was knocked down twice and took a beating.
Leonard's third comeback was ill-advised, but not enough to get him on this list. However, in 1999 he returned for a fourth time, at age 40, to face Hector Camacho.
This time Leonard suffered a Round 5 TKO. It was completely unnecessary punishment for him to absorb and a regrettable loss on his resume.